Alkyloxyacetyl compound of pyrocatechinmonoethyl ether.



. 'unirnn STATES PATENT OFFICE.

RUDOLPH BERENDES, OF ELBERFELD, GERMANY, ASSIGNOR TO FARBEN- FABRIKEN VORM. FRIEDR. BAYER & (30., OF ELBERFELD, GERMANY,

A- CORPORATION OF GERMANY.

ALKYLOXYACETYL COMPOUND F PYliOCATECHlNMONOETHYL ETHER.

Specification of Letters Patent.

Application filed March 31, 1906. Serial No. 509,096.

To aZZ whom it may concern.-

Be it known that I, RUDOLPH BERENDES, v

doctor of hilosophy, chemist, a citizen of the German Empire, residing at Elberfeld, Germany, Kingdom of Prussia, have invented new and useful Improvements in Alkyloxyacetyl Compounds of Pyrocatechin ethers, of which the following is a specification.

My invention -relates-to the production of new pharmaceutical products, which are chemically alkyloxyacetyl compounds of pyrocatechinmonoalkyl ethers, such as guaiacol,

creosol, pyrocatechinmonoethyl ether or the like, and which according to my researches possess valuable therapeutic properties, espe cially for the treatment of tuberculosis, and the absence of any odor, their freedom from irritation, non-toxicity, and ability of being easily reabsorbed render their outward application highly satisfactory, an average dose being between one to three grams for one ex ternal application.

The process for producing the new compounds consists in treating the above-mentioned pyrocatechinmonoalkyl others with alkyloxy acetic acids or derivatives thereof,

-' such as ethoxy or methox acetic acid, eth

oxyacetyl chlorid, or the ike, insuch manner as to produce esterification. The new products thus produced are colorless liquids soluble in alcohol and ether. When reacted up on by dilute caustic alkalies they are split u into alkyloxy acetic acid and the correspon ing pyrocatechinmonoalkyl ether.

In carrying out my process practically I .can roceed as follows, the parts being by weig t: One hundredand twenty-four parts of guaiacol and fort are dissolved in one t ousand parts of water, and to the resulting solution one hundred and twenty-two and one-half parts of ethoXy acetyl chlorid are added. After the chlorid has entered into reaction the mixture is shaken with ether, which will extract the new ester. The ethereal solution is then-se arated'fro'm the water, shaken with high ydilute caustic soda to remove unchanged guaiacol, and dried. The ether is driven off and the residue is distilled in cacao.

parts of caustic soda The new compound thus obtained having the formula:

is a limpid oil which boils at 150 centigrade under a pressure of about ten millimeters. It is easily soluble in alcohol and ether and is split up into ethoxy acetic acid and guaiacol when reacted upon bydilute caustic alkalies.

The process is carried out in an analogous manner on using-other alkyloxy acetic acids or derivatives thereof, such as methoxy acetic acid, methoxy acetyl chlorid, or other pyrocatechinmonoalkvl ethers, such as creosol, pyrocatechinmonothyl ether, &c.

Having now described my invention and in what manner the same is to be performed, what I claim as new, and desire to secure by Letters Patent, is

1. The herein-described new alkyloxy acetyl compounds of pyrocatechinmonoalkyl ethers, obtainable by the action of alkyloxy acetyl chlorid on pyrocatechinmonoalkyl ethers, being colorless ligluids soluble in ether Patentecl June 5, 1906. v

ing valuable therapeutic properties, substan- I tially as hereinbefore described.

In .testimony whereof I have hereunto set myhand in the presence of two subscribing witnesses.

RUDOLPH BERENDES: Witnesses! 7 O'r'ro Koivro, ARTHUR MATTnAUs. 

